CH253179A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253179A CH253179A CH253179DA CH253179A CH 253179 A CH253179 A CH 253179A CH 253179D A CH253179D A CH 253179DA CH 253179 A CH253179 A CH 253179A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- aliphatic
- aminocarboxamide
- acylated
- acetyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 4
- 125000001931 aliphatic group Chemical group 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000009835 boiling Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines acylierten, aliphatisehen Aminocarbonsäureamids. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäure- amids. Das Verfahren ist dadurch gekenn- zeiehnet, dass N-Acetyl-a-amino-n-buttersäure- dimethylamid propyliert wird.
Das N-Acetyl-a-(n-propylamino)-n-butter- s-iiui@ediiuetliylamid der Formel
EMI0001.0016
bildet eine farblose Flüssigkeit vom Siede punkt 129 unter 0,31 mm. Die neue Verbin dung soll therapeutische Verwendung finden.
<I>Beispiel:</I> \38,8 Teile a-Amino-n-buttersäuredimethyl- amid werden in 200 Teilen Äther gelöst und unter Rühren und Kühlen 7,8 Teile Acetyl- clilorid zugetropft. Nach 2stündigem Rühren wird vom a-Amino-n-buttersäi.redimethyl- amid-ehlorhydrat filtriert, vom Äther durch Destillation befreit und das Produkt fraktio niert: Siedepunkt 170 bis 172 unter 0,2 mm.
15,8 Teile des erhaltenen N-Acetyl-a-amino- n-buttersäuredimethylami.ds in 200 Teilen 1vIol werden mit 4 Teilen Natriumamid einige Zeit zum Sieden erhitzt. Nach dem Abkühlen wird mit 25 Teilen Propylbromid versetzt und im Druckgefäss auf 150 bis 160 erhitzt. Das Reaktionsprodukt wird mit ge sättigter Kalilauge durchgeschüttelt und die Xylollösung abgetrennt.
Nach dem Abdestil- lieren des Xylols wird der Rückstand im Hochvakuum rektifiziert. Die neue Verbin dung zeigt den Siedepunkt 129 unter 0,31 mm und ist leicht löslich in Wasser und organi schen Lösungsmitteln.
Process for the preparation of an acylated, aliphatic aminocarboxamide. The subject of the present additional patent is a process for the preparation of an acylated, aliphatic aminocarboxylic acid amide. The process is characterized in that N-acetyl-a-amino-n-butyric acid dimethylamide is propylated.
The N-acetyl-a- (n-propylamino) -n-butter- s-iiui @ ediiuetliylamid of the formula
EMI0001.0016
forms a colorless liquid with a boiling point of 129 below 0.31 mm. The new connec tion should find therapeutic use.
<I> Example: </I> \ 38.8 parts of a-amino-n-butyric acid dimethyl amide are dissolved in 200 parts of ether, and 7.8 parts of acetyl chloride are added dropwise with stirring and cooling. After stirring for 2 hours, the α-amino-n-buttersäi.redimethyl amide ehlorhydrat is filtered off, the ether is removed by distillation and the product is fractionated: boiling point 170 to 172 below 0.2 mm.
15.8 parts of the N-acetyl-a-amino-n-buttersäuredimethylami.ds obtained in 200 parts of 1vIol are heated to boiling for some time with 4 parts of sodium amide. After cooling, 25 parts of propyl bromide are added and the mixture is heated to 150 to 160 in a pressure vessel. The reaction product is shaken with saturated potassium hydroxide solution and the xylene solution is separated off.
After the xylene has been distilled off, the residue is rectified in a high vacuum. The new compound has a boiling point of 129 below 0.31 mm and is easily soluble in water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253179T | 1942-12-18 | ||
| CH244952T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253179A true CH253179A (en) | 1948-02-15 |
Family
ID=25729005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253179D CH253179A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253179A (en) |
-
1942
- 1942-12-18 CH CH253179D patent/CH253179A/en unknown
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